Water → 2-Phenylpiperazine

HRID 130583

Reaktionsgleichung

Reaktionsgleichung von HRID 130583
O=[C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:6][CH2:5][CH2:4][NH:3]1.O.[OH-].[Na+]>C1COCC1>[C:8]1([CH:7]2[CH2:2][NH:3][CH2:4][CH2:5][NH:6]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2506813-Phenylpiperazin-2-one

Produkt 1

HCID 2506732-PhenylpiperazineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Oxo-3-phenyl-piperazine (1.76 g, 10 mmol), in 30 mL of anhydrous THF was added dropwise to a 20 mL (20 mmol) of 1M solution of LiAH4 in THF, and the mixture was stirred at room temperature for 24 h. After workup (water, 20% NaOH addition to destroy excess LiAH4), the mixture was filtered and the filter cake was reextracted with ethyl acetate. The combined organic filtrate and extracts were dried over MgSO4, filtered and evaporated to give an slightly yellow solid that was purified by silica gel column chromatography (CHCl3:MeOH:NH4OH/9:1:0.1). The reduced product was isolated as a colorless solid (960 mg, 6 mmol, 60%). 1H NMR (CDCl3): δ 2.69 (1H, t, J=11.3), 2.85-3.10 (7H, m), 3.76 (1H, br d, J=8.9), 7.21-7.38 (5H, m). mp (free base): 79°-81° C.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. dry with materialThe combined organic filtrate and extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give an slightly yellow solid
  6. customthat was purified by silica gel column chromatography (CHCl3:MeOH:NH4OH/9:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-e66ccd1c13384e0e82a1431d1d957e84
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381822B2

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